What is the biggest red flag you've ever experienced in a relationship?

I went on a few dates with a guy who is a high school history teacher. He was obsessed with status and how much he spent on things. He bragged about his $10,000 watch and his $40,000 car. He loved to tell me how much he spent on clothes and his TV. Now this type of personality is a major red flag. He is a teacher and a fairly new one in my town. He has his masters so he makes more than others who are starting out. No way he makes more than $40,000 in Tennessee as a teacher. He is either a trust fund baby or has crippling debt. This personality also proves that little things you do for them won't matter it's only the money you spend that measures worth.

Men who brag or find a reason to talk about the amount of money they're spending on something unnecessarily irk me. It's one thing if he's talking to you in confidence, it's another thing if he just met you or he's just throwing out numbers to seem like some big cheese.

It's obvious that 1. He is quite superficial and shallow and, most importantly 2. He doesn't know me well enough to know that I really don't care about how much money he's bringing in to pay for this or that habit or luxury.

Unless he's my bf and he's sharing this personal info that I'll clearly need to know, I don't need to hear about it.

So I dated this girl for a little while while I was in the army. I never took or wanted to take this relationship seriously from the get go for a couple of reasons. First and foremost, I was getting out of the army in 9 months, secondly, she was a local. Service members should always be leery of local girls who want to date them. It's not always the case, but sometimes (often enough to cause concern) they have ulterior motives (i.e. , trapping you in a relationship with a pregnancy, using you to live that sort-of cozy military spouse lifestyle, or sometimes they take your money and run). Anyhow, she was a little strange in bed. Like she had this weird phobia of cum, she treated it like it was hot lead. It couldn't get on her and it was not allowed near or around her mouth. But she was so serious that I cum inside her because she had a Nuva ring. Well I told her I didn't want to take that kind of a chance, so she told me I would have to start wearing condoms then if I was so nervous. One day she had a condom ready for me and it set off all sorts of red flags. I went to the bathroom, ran it under the sink, and wouldn't you know it sprung a leak. I noped the fuck out of there really fast. Flash forward a few weeks later and she shows up to drop off a few of my things she had. I stayed by and shot the shit with her for a minute and this other guy starts approaching us and he just climbs right on in the car and gave me this look like he had somehow won some sort of competition with me. He won alright, she was pregnant weeks later.

Dated a girl who was super paranoid because her last boyfriend turned into a psycho stalker. And the boyfriend before that was also a psycho stalker. Thought this was kinda weird but didn't think anything of it. We broke up fairly quickly after that, amicably.

Fast forward like four years, I'm engaged to be married, and out of the blue she suddenly starts sending me emails and FB messages to "stop stalking her." Also threatens to tell my fiancee that I'm gay because she found shemale porn on my computer once back when we were dating.

So... yeah. That old saying, if you smell shit everywhere you go, check your shoes? It applies.